US2164393A - Lubricating oil - Google Patents
Lubricating oil Download PDFInfo
- Publication number
- US2164393A US2164393A US74388A US7438836A US2164393A US 2164393 A US2164393 A US 2164393A US 74388 A US74388 A US 74388A US 7438836 A US7438836 A US 7438836A US 2164393 A US2164393 A US 2164393A
- Authority
- US
- United States
- Prior art keywords
- lubricant
- extreme
- thio
- lubricating oil
- substituent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000010687 lubricating oil Substances 0.000 title description 7
- 239000000314 lubricant Substances 0.000 description 32
- 150000003568 thioethers Chemical class 0.000 description 19
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- -1 sulphur compound Chemical class 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- This invention is for improvements in or relating to lubricants which are to be used under conditions which tend to disrupt the lubricant mechanism.
- extreme-pressure lubricants originally consisted of lubricating oil which contained sulphur, either in the form of flowers of sulphur or as a colloidal dispersion.
- the sulphur was liable to precipitation and it was later proposed to prepare these extreme-pressure lubricants by treating a fatty oil, for example an animal oil, with thionylchloride or with similar reagents, such as sulphur monochloride, sulphur dichloride etc., and then adding the product of this reaction to a mineral oil.
- an extreme-pressure lubricant comprises a lubricating oil or grease having dispersed therein a small quantity of a thin-ether. It has been found that the desired effects may be obtained by employing the thioether in quantities up to about 2% by weight of theoiL I
- a feature of the invention consists in that the-thio-ether comprises two aromatic radicals. Preferably, at least one of said aromatic radicals contains either a hydroxyl substituent or a carboxyl (or ester) substituent.
- each of said aromatic radicals contains both a hydroxyl substituent and a carboxyl (or ester) substituent.
- the hydroxyl substituents' are located. in the para-position in the aromatic-radical.
- a stillifu" her feature of the invention consists in that said thio-ether contains two aliphatic radicals. Either one or both of said aliphatic radicals contains either an hydroxyl substituent or a carboxyl (or ester) substituent or both.
- the film-rupture strength was found to be raised to the extremely high value of 15,000 pounds per square inch, a remarkable increase over the value obtained with the puremineral oil which, in the Almen tester, gave a film-rupture strength of between 3,000 to 4,000 pounds per square inch.
- the extreme-pressure lubricants hitherto prepared have in general required at least 5% of a sulphur base (prepared by reacting sulphur chloride with the fatty oil) in order to produce a comparable increase in the film rupture strength of the oil.
- the invention also includes within its scope, the method of preparing extreme-pressure lubricants which comprises dispersing thio-ethers of the above-mentioned class in a lubricating oil or grease in quantities, which are accurately controllable.
- the invention is not restricted to the employment of particular proportions of the thio-ethers since within certain limits the film-rupture strength of the lubricant may be adjusted to a desired value in accordance with the quantity of thio-ether added in order to render the lubricant suitable for any special use or mechanism.
- An extreme-pressure lubricant comprising a lubricant having dispersed therein between 0.1% and 2% of a thio-ether comprising two aromatic radicals at least one of which aromatic radicals contain an ester substituent.
- An extreme-pressure lubricant comprising a lubricant having dispersed therein between 0.1% and 2% of a thio-ether comprising two aromatic radicals at least one of which aromatic radicals contains an hydroxyl substituent and an ester substituent.
- Anextreme-preSsure lubricant comprising a lubricant having dispersed therein between 0.1% and 2% of a thio-ether comprising two aromatic radicals at least one of which aromatic radicals contains an hydroxyl substituent in the paraposition and an ester substituent.
- An extreme-pressure lubricant comprising a lubricant having dispersed therein between 0.1% and 2% of a thio-ether comprising two aromatic radicalsboth of which aromatic radicals contain an hydroxyl substituent in the para-position and an ester substituent,
- An extreme-pressure lubricant comprising a lubricating oil having-dispersed therein between 0.l% and 2% of a thio-ether having an ester-substituent.
- An extreme-pressure lubricant comprising a mineral lubricating oil having dispersed therein up to 2% of bis (B-carbomethoxy 4-hydroxyphenyl) thio-ether.
- An extreme-pressure lubricant comprising a mineral lubricating oil having dispersed therein about 1% of the thio-ether formed by the condensation of ethyl benzoate in the presence of thionyl chloride and copper dust.
- An extreme-pressure lubricant comprising a mineral lubricating oil having dispersed there: in about 1% of the thio-ether formed by the condensation of ethyl phthalate in the presence of thionyl chloride and copper dust.
- An extreme-pressure lubricant comprising a .lubricant having dispersed therein between 0.1% and 2% of a thioether having a substituentgroup--COOX wherein X is a radical of the group consisting of aliphatic radicals.
- An extreme-pressure lubricant comprising a lubricant having dispersed therein between 0.1% and 2% of a thioether each radical of which contains a substituent-group-COOX in which X is of the group consisting of aliphatic radicals.
- a lubricant comprising a lubricating oil having dispersed therein an extreme-pressure agent consisting of a thioether having a substituen't-groupCOOX in which X is of the group consisting of aliphatic radicals.
- a lubricant comprising a lubricating oil having dispersed therein between 0.1% and 2% of an extreme-pressure agent consisting of a thioether each radical of which contains a substituent-group-COOX in which X is of the group consisting of aliphatic radicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11629/35A GB455235A (en) | 1935-04-15 | 1935-04-15 | Improvements in or relating to lubricating oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2164393A true US2164393A (en) | 1939-07-04 |
Family
ID=9989788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US74388A Expired - Lifetime US2164393A (en) | 1935-04-15 | 1936-04-14 | Lubricating oil |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2164393A (enrdf_load_stackoverflow) |
| BE (1) | BE415008A (enrdf_load_stackoverflow) |
| DE (1) | DE680406C (enrdf_load_stackoverflow) |
| FR (1) | FR804869A (enrdf_load_stackoverflow) |
| GB (1) | GB455235A (enrdf_load_stackoverflow) |
| NL (1) | NL42443C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451895A (en) * | 1946-06-08 | 1948-10-19 | Shell Dev | Synthetic grease |
| US2601063A (en) * | 1948-09-24 | 1952-06-17 | Standard Oil Dev Co | Glycol esters of alkyl-mercapto-carboxylic acids |
| DE856686C (de) * | 1943-07-22 | 1952-11-24 | Hoechst Ag | OEle fuer die Metallbearbeitung |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB757241A (en) * | 1953-09-17 | 1956-09-19 | Wakefield & Co Ltd C C | Improvements in or relating to lubricating compositions |
-
0
- BE BE415008D patent/BE415008A/xx unknown
- NL NL42443D patent/NL42443C/xx active
-
1935
- 1935-04-15 GB GB11629/35A patent/GB455235A/en not_active Expired
-
1936
- 1936-04-10 DE DEW98543D patent/DE680406C/de not_active Expired
- 1936-04-10 FR FR804869D patent/FR804869A/fr not_active Expired
- 1936-04-14 US US74388A patent/US2164393A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE856686C (de) * | 1943-07-22 | 1952-11-24 | Hoechst Ag | OEle fuer die Metallbearbeitung |
| US2451895A (en) * | 1946-06-08 | 1948-10-19 | Shell Dev | Synthetic grease |
| US2601063A (en) * | 1948-09-24 | 1952-06-17 | Standard Oil Dev Co | Glycol esters of alkyl-mercapto-carboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| GB455235A (en) | 1936-10-15 |
| FR804869A (fr) | 1936-11-04 |
| NL42443C (enrdf_load_stackoverflow) | |
| BE415008A (enrdf_load_stackoverflow) | |
| DE680406C (de) | 1939-08-29 |
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